AU669604B2 - Vapor phase chlorination of difluoromethyl methyl ether - Google Patents
Vapor phase chlorination of difluoromethyl methyl ether Download PDFInfo
- Publication number
- AU669604B2 AU669604B2 AU57778/94A AU5777894A AU669604B2 AU 669604 B2 AU669604 B2 AU 669604B2 AU 57778/94 A AU57778/94 A AU 57778/94A AU 5777894 A AU5777894 A AU 5777894A AU 669604 B2 AU669604 B2 AU 669604B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- accordance
- hoch
- fluorinated
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000005660 chlorination reaction Methods 0.000 title claims description 21
- CGZAMBNIGLUBRY-UHFFFAOYSA-N difluoro(methoxy)methane Chemical compound COC(F)F CGZAMBNIGLUBRY-UHFFFAOYSA-N 0.000 title claims description 16
- 239000012808 vapor phase Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 16
- 150000001875 compounds Chemical group 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 150000005218 dimethyl ethers Chemical class 0.000 claims description 8
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 8
- -1 alkali metal methoxide Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 101000831256 Oryza sativa subsp. japonica Cysteine proteinase inhibitor 1 Proteins 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IOCGMLSHRBHNCM-UHFFFAOYSA-N difluoromethoxy(difluoro)methane Chemical compound FC(F)OC(F)F IOCGMLSHRBHNCM-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003682 fluorination reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 231100000357 carcinogen Toxicity 0.000 description 4
- 239000003183 carcinogenic agent Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- VBPQHEWBJDVOBN-UHFFFAOYSA-N 1-(1,1-difluoroethoxy)-1,1-difluoroethane Chemical compound CC(F)(F)OC(C)(F)F VBPQHEWBJDVOBN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 235000020004 porter Nutrition 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- RNVQRVSELABAHN-UHFFFAOYSA-N dichloromethoxy(difluoro)methane Chemical compound FC(F)OC(Cl)Cl RNVQRVSELABAHN-UHFFFAOYSA-N 0.000 description 1
- CHRXLMMVJKAYGJ-UHFFFAOYSA-N difluoro(fluoromethoxy)methane Chemical compound FCOC(F)F CHRXLMMVJKAYGJ-UHFFFAOYSA-N 0.000 description 1
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/025,009 US5278342A (en) | 1992-03-25 | 1993-03-15 | Vapor phase chlorination of difluoromethyl methyl ether |
| US025009 | 1993-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5777894A AU5777894A (en) | 1994-09-22 |
| AU669604B2 true AU669604B2 (en) | 1996-06-13 |
Family
ID=21823552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU57778/94A Ceased AU669604B2 (en) | 1993-03-15 | 1994-03-11 | Vapor phase chlorination of difluoromethyl methyl ether |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPH06298693A (enrdf_load_stackoverflow) |
| KR (1) | KR100285073B1 (enrdf_load_stackoverflow) |
| CN (1) | CN1054115C (enrdf_load_stackoverflow) |
| AU (1) | AU669604B2 (enrdf_load_stackoverflow) |
| BR (1) | BR9401152A (enrdf_load_stackoverflow) |
| CA (1) | CA2118828A1 (enrdf_load_stackoverflow) |
| MY (1) | MY110487A (enrdf_load_stackoverflow) |
| TW (1) | TW252973B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6974718B2 (ja) * | 2017-01-13 | 2021-12-01 | セントラル硝子株式会社 | １，２，２，２−テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法 |
| US10683252B2 (en) | 2016-12-29 | 2020-06-16 | Central Glass Company, Limited | Production method for 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) |
| WO2018123649A1 (ja) * | 2016-12-29 | 2018-07-05 | セントラル硝子株式会社 | １，２，２，２－テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法 |
| JP6886104B2 (ja) | 2016-12-29 | 2021-06-16 | セントラル硝子株式会社 | ハロゲン化α−フルオロエーテル類の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA917855B (en) * | 1990-10-02 | 1993-03-31 | Grace W R & Co | Synthesis of fluorinated dimethyl ethers |
-
1994
- 1994-03-11 AU AU57778/94A patent/AU669604B2/en not_active Ceased
- 1994-03-11 CA CA002118828A patent/CA2118828A1/en not_active Abandoned
- 1994-03-14 CN CN94104805A patent/CN1054115C/zh not_active Expired - Fee Related
- 1994-03-15 KR KR1019940005112A patent/KR100285073B1/ko not_active Expired - Fee Related
- 1994-03-15 BR BR9401152A patent/BR9401152A/pt not_active IP Right Cessation
- 1994-03-15 JP JP6044064A patent/JPH06298693A/ja active Pending
- 1994-03-16 MY MYPI94000614A patent/MY110487A/en unknown
- 1994-04-26 TW TW083103735A patent/TW252973B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| BR9401152A (pt) | 1994-11-01 |
| MY110487A (en) | 1998-08-29 |
| KR940021492A (ko) | 1994-10-19 |
| KR100285073B1 (ko) | 2001-04-02 |
| CA2118828A1 (en) | 1994-09-16 |
| AU5777894A (en) | 1994-09-22 |
| JPH06298693A (ja) | 1994-10-25 |
| TW252973B (enrdf_load_stackoverflow) | 1995-08-01 |
| CN1100711A (zh) | 1995-03-29 |
| CN1054115C (zh) | 2000-07-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |